Plus if you think about it if the property is maintained the price is likely not gonna go down and so you should take into account equity gained.

Does it cost a lot more to maintain a 2,500sf house in Palo Alto renting for $10k/month compared to a 2,500sf house in Elk Grove renting for $1,800/month?

No need to hire a chimney sweep every six months, provide & maintain fire extinguishers, extra CO alarms, this list goes on.On this one, I would be aggressively defensive. 

Meticulously maintained, all brick, historic home on coveted street a few minute walk from OSU campus. 5-6 bedrooms, only one bath and not so easy to turn into duplex.

Building a quality trustworthy team is not always simple and it takes work to maintain the team (even local takes work to maintain a quality team).As for buying your primary residence I have two considerations: 1) how long do you plan to live in the area 2) how are the long term appreciation outlook (in LA the long-term appreciation outlook historically has been excellent). 

It's ridiculous how much time it actually takes to maintain the building once you got someone in there running it for you.That way you have all the free time in the world to travel, stay home, do what you want, spend more time with your family, work on more apartment deals and the list of benefits goes on and on.

If I have owned and maintained a property for 30 years, I know everything about it.

But, when it comes to finishes (light fixtures, plumbing fixtures, appliances, cabinets, etc), I prefer to maintain control over the look and feel of the final product.

I am wanting to rent it out for maybe 1100-$1200/month hopefully making maybe a 100-150/month cash flow and saving the rest for maintainance.

I purchased and managed 6 while working FT, but QUIT my job to focus on RE..I'm building and maintaining my portfolio...At some point, I will turn over to PM, but I enjoy handling the people aspect of my business!!